One of the more constant struggles when it comes to upgrading your life is the area of clothes. Fashions change so goddamned often that by the time you have a handle of what’s supposed to be “cool”, it’s already become retro and everybody’s moved on to other things.
And let me tell you, the struggle to keep up with fashion leads to some hideous mistakes. Watch a few movies from the 80s and 90s and look at what people thought was cool. How about some giant shoulder pads and unstructured jackets? Maybe a few comedically oversized suits? Ooh, how about Jams? Anyone for a Jams revival?
If you want a look that lasts beyond the constant whirlwind of change that is haute couture, you need to quit paying attention to fashion and start trying to develop your style instead.
Y’see, fashion is temporary. It changes with every passing fad.
Style is forever.
Here’s how to develop yours.
Know Who You Are
Your style sends a message to the people around you. It tells them who you are. It gives them an idea of what to expect from you and what your life is like.
For example, take Andre 3000:
This is a man who puts a lot of care into his look – and likely into his life. And yet, those playful touches tell you that he’s also a man who likes to take risks and have fun. The outfit says “I have money” without bludgeoning you over the head like Sean Combes’ sharkskin suits do. It has style but also subtlety; this is a man with confidence.
All of this from a set of clothes.
Your style outward indication of your identity. This is one of the reasons why I advocate the adoption of sexy stereotypes; people are already judging you by visual short-hand so why not take advantage of that? As much as we want people to love us for who we are on the inside, this is a process that takes time and that first impression can be made in an instant.
You want to use your personal style to maximum effect. You want people to know who – and what – you are within a split second of seeing you.
So of course, you need to know who you are and how to control the message you’re sending to others.
This means that your style needs to reflect who you are. If you’re the corporate office type who’s trying to dress like an extra from Sons of Anarchy, all you’re going to do is make people wonder who you think you’re fooling. Similarly, punk rockers don’t do well with Saville Rowe suits.
Figure out who you are at your core – that’s your building block for style.
What They’re Going To Notice
Part of style is controlling what people are going to pick up on, which is where you want to spend the majority of your attention and care. Let’s say that you’re rocking some snazzy shoes, perfectly fit designer jeans and an expensive-yet-understated vintage wristwatch. Your hair is perfect. However, for some reason you’ve decided that you’re going to compliment this with the shame-tarp1 you picked up for free at PAX East. Or maybe you decided to wear your most bro-tastic t-shirt; the one you bought because you thought it was hilarious to wear to parties in college.
Pop quiz: are they going to think “There goes a man who knows how to live life to the fullest?” Or are they going to think “Woah, dude’s a dipshit?”
Basic rule of style: the last thing you put on is the first thing that people notice. No matter how styling your pants may be, your worn-out shirt and slept-in jacket are going to be telling people that you just don’t give a damn. If you’re spending all of your attention on the wrong parts of your clothes, all you’re doing is wasting time and effort fighting the message your style is sending.
In practical terms, the heirarchy of style noticeability breaks down thusly:
- Socks and underwear
The higher on the list, the higher the priority it is for your wardrobe.
Think about it: where’s the first place we look when we see somebody, especially somebody of the opposite sex?
No, boobs are the second thing. Also: you’re an asshole.
We look at the face and work our way outward from there.
The lower on the list, the less likely people are to notice. As nice as, say, designer jeans are, most people will only notice the color and the cut unless you’re talking to dedicated label snobs, fashionistas or there’s just something so outlandish about them – painted-on tight, overly decorated rear pockets, slacks with pleats2 – that they can’t be ignored. Similarly, by the time you’re down to your underwear, unless there’s something that’s incredibly outré, nobody will care.
(That being said: guys – boxers or boxer briefs. Period. No tighty-whities. Bikini briefs are verboten. And if you’re wearing a thong, then it better be because you’re dressed like a fireman and wearing break-away pants. )
Note: If you’re a man and you’re talking to women, shoes rockets up to #2. Women always, always, always notice your shoes.
- Shame Tarp (noun): a shirt, given away for free – usually by gaming companies – at conventions as a form of advertising. Usually, but not necessarily over-sized [↩]
- NO. Just… no. [↩]